Abstract
Fullerenes are popular electron acceptors for their high electron affinity and low reorganization energy . Photoexcitation in endohedral fullerenes (EMFs)-based donor–acceptor dyads have been comprehensively studied in the past decade. Different donor moieties such as ferrocene, exTTF, zinc tetraphenylporphyrine, triphenylamine were successfully used to construct EMF-based donor–acceptor dyads, and the charge/energy transfer mechanisms between versatile donors and EMF acceptors were extensively investigated. Besides, the charge carrier mobility of solid EMFs and applications of EMFs in organic photovoltaics (OPVs) and photoelectrochemical (PEC) cells were also reviewed.
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References
He Y, Li Y (2011) Fullerene derivative acceptors for high performance polymer solar cells. Phys Chem Chem Phys 13:1970–1983
(a) Popov AA, Yang S, Dunsch L (2013) Endohedral fullerenes. Chem Rev 113:5989–6113; (b) Lu X, Feng L, Akasaka T et al (2012) Current status and future developments of endohedral metallofullerenes. Chem Soc Rev 41:7723–7760
Pinzón JR, Plonska-Brzezinska ME, Cardona CM et al (2008) Sc3N@C80-ferrocene electron-donor/acceptor conjugates as promising materials for photovoltaic applications. Angew Chem Int Ed Engl 47:4173–4176
Guldi DM, Maggini M, Scorrano G et al (1997) Intramolecular electron transfer in fullerene/ferrocene based donor–bridge–acceptor dyads. J Am Chem Soc 119:974–980
Pinzón JR, Cardona CM, Herranz MA et al (2009) Metal nitride cluster fullerene M3N@C80 (M = Y, Sc) based dyads: synthesis, and electrochemical, theoretical and photophysical studies. Chem Eur J 15:864–877
Takano Y, Herranz MA, Martin N et al (2010) Donor-acceptor conjugates of lanthanum endohedral metallofullerene and pi-extended tetrathiafulvalene. J Am Chem Soc 132:8048–8055
Takano Y, Obuchi S, Mizorogi N et al (2012) Stabilizing ion and radical ion pair states in a paramagnetic endohedral metallofullerene/pi-extended tetrathiafulvalene conjugate. J Am Chem Soc 134:16103–16106
Guldi DM, Feng L, Radhakrishnan SG et al (2010) A molecular Ce2@I(h)-C80 switch–unprecedented oxidative pathway in photoinduced charge transfer reactivity. J Am Chem Soc 132:9078–9086
Wolfrum S, Pinzon JR, Molina-Ontoria A et al (2011) Utilization of Sc3N@C80 in long-range charge transfer reactions. Chem Commun 47:2270–2272
Feng L, Radhakrishnan SG, Mizorogi N et al (2011) Synthesis and charge-transfer chemistry of La2@I(h)-C80/Sc3N@I(h)-C80-zinc porphyrin conjugates: impact of endohedral cluster. J Am Chem Soc 133:7608–7618
Feng L, Slanina Z, Sato S et al (2011) Covalently linked porphyrin-La@C82 hybrids: structural elucidation and investigation of intramolecular interactions. Angew Chem Int Ed Engl 50:5909–5912
Pinzón JR, Gasca DC, Sankaranarayanan SG et al (2009) Photoinduced charge transfer and electrochemical properties of triphenylamineIh-Sc3N@C80 donor–acceptor conjugates. J Am Chem Soc 131:7727–7734
Feng L, Rudolf M, Wolfrum S et al (2012) A paradigmatic change: linking fullerenes to electron acceptors. J Am Chem Soc 134:12190–12197
Takano Y, Obuchi S, Mizorogi N et al (2012) An endohedral metallofullerene as a pure electron donor: intramolecular electron transfer in donor–acceptor conjugates of La2@C80 and 11,11,12,12-tetracyano-9,10-anthra-p-quinodimethane (TCAQ). J Am Chem Soc 134:19401–19408
Liu B, Fang H, Li X et al (2015) Synthesis and photophysical properties of a Sc3N@C80-Corrole electron donor–acceptor conjugate. Chem Eur J 21:746–752
Feng L, Rudolf M, Trukhina O (2015) Tuning intramolecular electron and energy transfer processes in novel conjugates of La2@C80 and electron accepting subphthalocyanines. Chem Comm 51:330–333
Yang S, Fan L, Yang S (2003) Preparation, characterization, and photoelectrochemistry of Langmuir–Blodgett films of the endohedral metallofullerene Dy@C82 mixed with metallophthalocyanines. J Phys Chem B 107:8403–8411
Yang S, Yang S (2002) Preparation and film formation behavior of the supramolecular complex of the endohedral metallofullerene Dy@C82 with Calix[8]arene. Langmuir 18:8488–8495
Grimm B, Schornbaum J, Cardona CM et al (2011) Enhanced binding strengths of acyclic porphyrin hosts with endohedral metallofullerenes. Chem Sci 2:1530–1537
Hernandez-Eguia LP, Escudero-Adan EC, Pinzon JR et al (2011) Complexation of Sc3N@C80 endohedral fullerene with cyclic Zn-bisporphyrins: solid state and solution studies. J Org Chem 76:3258–3265
Tsuchiya T, Rudolf M, Wolfrum S et al (2013) Coordinative interactions between porphyrins and C60, La@C82, and La2@C80. Chem Eur J 19:558–565
Kawashima Y, Ohkubo K, Fukuzumi S (2012) Enhanced photoinduced electron-transfer reduction of Li+@C60 in comparison with C60. J Phys Chem A 116:8942–8948
Kawashima Y, Ohkubo K, Fukuzumi S (2013) Small reorganization energies of photoinduced electron transfer between spherical fullerenes. J Phys Chem A 117:6737–6743
Yamada M, Ohkubo K, Shionoya M et al (2014) Photoinduced electron transfer in a charge-transfer complex formed between corannulene and Li+@C60 by concave–convex π–π interactions. J Am Chem Soc 136:13240–13248
Supur M, Kawashima Y, Larsen KR et al (2014) Robust Inclusion Complexes of crown ether fused tetrathiafulvalenes with Li+@C60 to afford efficient photodriven charge separation. Chem Eur J 20:13976–13983
Taherpour A, Maleki-Noureini M (2013) Free energies of electron transfer, electron transfer kinetic theoretical and quantitative structural relationships and electrochemical properties studies of gadolinium nitride cluster fullerenes Gd3N@Cn in [X–UT–Y][Gd3N@Cn](n = 80, 82, 84, 86 and 88) Supramolecular Complexes. Fuller Nanotub Carbon Nanostruct 21:485–502
Ross RB, Cardona CM, Guldi DM et al (2009) Endohedral fullerenes for organic photovoltaic devices. Nat Mater 8:208–212
Ross RB, Cardona CM, Swain FB et al (2009) Tuning conversion efficiency in metallo endohedral fullerene-based organic photovoltaic devices. Adv Funct Mater 19:2332–2337
Liedtke M, Sperlich A, Kraus H et al (2011) Triplet exciton generation in bulk-heterojunction solar cells based on endohedral fullerenes. J Am Chem Soc 133:9088–9094
Yang S, Fan L, Yang S (2004) Langmuir–Blodgett Films of Poly(3-hexylthiophene) Doped with the endohedral metallofullerene Dy@C82: preparation, characterization, and application in photoelectrochemical cells. J Phys Chem B 108:4394–4404
Nuttall CJ, Hayashi Y, Yamazaki K et al (2002) Dipole dynamics in the endohedral metallofullerene La@C82. Adv Mater 14:293–296
Kubozono Y, Takabayashi Y, Shibata K et al (2003) Crystal structure and electronic transport of Dy@C82. Phys Rev B 67
Kareev IE, Bubnov VP, Laukhina EE et al (2003) Endohedral metallofullerenes M@C82 (M = La, Y): synthesis and transport properties. Carbon 41:1375–1380
(a) Kanbara T, Shibata K, Fujiki S et al (2003) N-channel field effect transistors with fullerene thin films and their application to a logic gate circuit. Chem Phys Lett 379:223–229; (b) Rikiishi Y, Kubozono Y, Hosokawa T et al (2004) Structural and electronic characterizations of two isomers of Ce@C82. J Phys Chem B 108:7580–7585; (c) Nagano T, Kuwahara E, Takayanagi T et al (2005) Fabrication and characterization of field-effect transistor device with C2v isomer of Pr@C82. Chem Phys Lett 409:187–191; (d) Kobayashi S, Mori S, Iida S et al (2003) Conductivity and field effect transistor of La2@C80 metallofullerene. J Am Chem Soc 125:8116–8117
Popok VN, Gromov AV, Jönsson M et al (2008) Electronic properties of thin films sublimed from La@C82 and Li@C60. NANO 03:155–160
(a) Sato S, Seki S, Honsho Y et al (2011) Semi-metallic single-component crystal of soluble La@C82 derivative with high electron mobility. J Am Chem Soc 133:2766–2771; (b) Sato S, Seki S, Luo G et al (2012) Tunable charge-transport properties of I(h)-C80 endohedral metallofullerenes: investigation of La2@C80, Sc3N@C80, and Sc3C2@C80. J Am Chem Soc 134:11681–11686
Sato S, Nikawa H, Seki S et al (2012) A co-crystal composed of the paramagnetic endohedral metallofullerene La@C82 and a nickel porphyrin with high electron mobility. Angew Chem Int Ed Engl 51:1589–1591
Sun Y, Maeda Y, Sezaimaru H et al (2014) Carrier transport properties of nanocrystalline Er3N@C80. J Appl Phys 116:034301
Li Z, Luo W, Zhang M et al (2013) Photoelectrochemical cells for solar hydrogenproduction: current state of promising photoelectrodes, methods to improve their properties, and outlook. Energy Environ Sci 6:347–370
Bard AJ, Stratmann M, Licht S (eds) (2002) Encyclopedia of electrochemistry. In: Semiconductor Electrodes and Photoelectrochemistry, vol 6. Wiley-VCH, Weinheim
(a) Miller B, Rosamilia JM, Dabbagh G et al (1991) Photoelectrochemical behavior of C60 films. J Am Chem Soc 113:6291–6293; (b) Licht S, Khaselev O, Ramakrishnan PA et al (1998) Fullerene photoelectrochemical solar cells. Sol Energ Mat Sol C 51:9–19; (c) Wei T, Shi Y, Zhai J et al (2000) Synthesis, monolayer fabrication and photoelectric conversion property of two pyrrolidinofullerene carboxylic acid derivatives. Chem Phys Lett 319:7–12
(a) Yang S, Yang S (2001) Photoelectrochemistry of Langmuir–Blodgett films of the endohedral metallofullerene Dy@C82 on ITO electrodes. J Phys Chem B 105:9406–9412; (b) Yang S, Fan L, Yang S (2004) Significantly enhanced photocurrent efficiency of a poly(3-hexylthiophene) photoelectrochemical device by doping with the endohedral metallofullerene Dy@C82. Chem Phys Lett 388:253–258
Xu Y, Guo J, Wei T et al (2013) Micron-sized hexagonal single-crystalline rods of metal nitride clusterfullerene: preparation, characterization, and photoelectrochemical application. Nanoscale 5:1993–2001
Acknowledgements
The research work was partially supported by National Basic Research Program of China (2011CB921400) and National Natural Science Foundation of China (21132007, 21371164).
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Zhen, J., Liu, Q., Yang, S. (2017). Photoexcitation in Donor–Acceptor Dyads Based on Endohedral Fullerenes and Their Applications in Organic Photovoltaics. In: Popov, A. (eds) Endohedral Fullerenes: Electron Transfer and Spin. Nanostructure Science and Technology. Springer, Cham. https://doi.org/10.1007/978-3-319-47049-8_5
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DOI: https://doi.org/10.1007/978-3-319-47049-8_5
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